Phenylalanyl adenylate

    WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H597762

CAS#: 35874-27-2

Description: Phenylalanyl adenylate is a bioactive chemical.

Chemical Structure

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Phenylalanyl adenylate
CAS# 35874-27-2
Instruction

Theoretical Analysis

Hodoodo Cat#: H597762
Name: Phenylalanyl adenylate
CAS#: 35874-27-2
Chemical Formula: C19H23N6O8P
Exact Mass: 494.13
Molecular Weight: 494.400
Elemental Analysis: C, 46.16; H, 4.69; N, 17.00; O, 25.89; P, 6.26

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Phenylalanyl adenylate; Phe-pA;

IUPAC/Chemical Name: (S)-2-amino-3-phenylpropanoic (((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphoric) anhydride

InChi Key: ZFNOOEXYTZPIQS-URQYDQELSA-N

InChi Code: InChI=1S/C19H23N6O8P/c20-11(6-10-4-2-1-3-5-10)19(28)33-34(29,30)31-7-12-14(26)15(27)18(32-12)25-9-24-13-16(21)22-8-23-17(13)25/h1-5,8-9,11-12,14-15,18,26-27H,6-7,20H2,(H,29,30)(H2,21,22,23)/t11-,12+,14+,15+,18+/m0/s1

SMILES Code: O=C([C@H](Cc1ccccc1)N)O[P@@](O)(OC[C@@H]2[C@H]([C@H]([C@H](n(cn3)c4c3c(N)ncn4)O2)O)O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 494.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Reshetnikova L, Moor N, Lavrik O, Vassylyev DG. Crystal structures of phenylalanyl-tRNA synthetase complexed with phenylalanine and a phenylalanyl-adenylate analogue. J Mol Biol. 1999 Apr 2;287(3):555-68. PubMed PMID: 10092459.

2: Fishman R, Ankilova V, Moor N, Safro M. Structure at 2.6 A resolution of phenylalanyl-tRNA synthetase complexed with phenylalanyl-adenylate in the presence of manganese. Acta Crystallogr D Biol Crystallogr. 2001 Nov;57(Pt 11):1534-44. Epub 2001 Oct 25. PubMed PMID: 11679717.

3: Moor N, Kotik-Kogan O, Tworowski D, Sukhanova M, Safro M. The crystal structure of the ternary complex of phenylalanyl-tRNA synthetase with tRNAPhe and a phenylalanyl-adenylate analogue reveals a conformational switch of the CCA end. Biochemistry. 2006 Sep 5;45(35):10572-83. PubMed PMID: 16939209.

4: Ibba M, Johnson CM, Hennecke H, Fersht AR. Increased rates of tRNA charging through modification of the enzyme-aminoacyl-adenylate complex of phenylalanyl-tRNA synthetase. FEBS Lett. 1995 Jan 30;358(3):293-6. PubMed PMID: 7843418.

5: Yamamoto N, Ishigami M, Kinjo M. Catalytic mechanism of histone in peptide formation from phenylalanyl adenylate. Orig Life. 1982 Dec;12(4):355-9. PubMed PMID: 7185044.

6: Ishigami M, Tonotsuka-Ohta N, Nagano K, Kinjo M. Effect of polynucleotides and a basic protein on the condensation of phenylalanyl adenylate. Orig Life. 1980 Sep;10(3):293-9. PubMed PMID: 7191079.

7: Moor N, Lavrik O, Favre A, Safro M. Prokaryotic and eukaryotic tetrameric phenylalanyl-tRNA synthetases display conservation of the binding mode of the tRNA(Phe) CCA end. Biochemistry. 2003 Sep 16;42(36):10697-708. PubMed PMID: 12962494.

8: Fu H, Han B, Zhao YF, Tu GZ, Xu L, Lu Q, Wang JZ, Xiao HZ. Synthesis and hydrolysis of a phenylalanyl adenylate pentacoordinated phosphorane. Bioorg Chem. 2003 Apr;31(2):122-8. PubMed PMID: 12729569.

9: Rapaport E, Yogeeswaran G, Zamecnik PC, Remy P. Covalent modification of phenylalanyl-tRNA synthetase with phenylalanine during the amino acid activation reaction catalyzed by the enzyme. J Biol Chem. 1985 Aug 15;260(17):9509-12. PubMed PMID: 3848435.

10: Lacey JC Jr, Senaratne N, Mullins DW Jr. Hydrolytic properties of phenylalanyl- and N-acetylphenylalanyl adenylate anhydrides. Orig Life Evol Biosph. 1984;15(1):45-54. PubMed PMID: 11541967.

11: McMasters DR, Vedani A. Ochratoxin binding to phenylalanyl-tRNA synthetase: computational approach to the mechanism of ochratoxicosis and its antagonism. J Med Chem. 1999 Aug 12;42(16):3075-86. PubMed PMID: 10447951.

12: Guédon G, Ebel JP, Remy P. Yeast phenylalanyl-tRNA synthetase: evidence for the formation of ADP by phosphorolysis of enzyme-bound aminoacyladenylate. Biochimie. 1987 Nov-Dec;69(11-12):1175-81. PubMed PMID: 3129022.

13: von der Haar. Phenylalanyl-tRNA synthetase from baker's yeast: specificity and quantitation of affinity elution with tRNA. Hoppe Seylers Z Physiol Chem. 1976 Jun;357(6):819-23. PubMed PMID: 783032.

14: Boutorin AS, Gordienko VA, Lavrik OI, Moor NA. tRNAPhe deprived of 3'-terminal adenosyl residue does not stimulate adenosine aminoacylation catalyzed by phenylalanyl-tRNA synthetase from Escherichia coli. FEBS Lett. 1988 Sep 26;238(1):211-3. PubMed PMID: 3049157.

15: Harnett SP, Lowe G, Tansley G. Mechanism of activation of phenylalanine and synthesis of P1, P4-bis(5'-adenosyl) tetraphosphate by yeast phenylalanyl-tRNA synthetase. Biochemistry. 1985 Jun 4;24(12):2908-15. PubMed PMID: 3893531.

16: Baltzinger M, Lin SX, Remy P. Yeast phenylalanyl-tRNA synthetase: symmetric behavior of the enzyme during activation of phenylalanine as shown by a rapid kinetic investigation. Biochemistry. 1983 Feb 1;22(3):675-81. PubMed PMID: 6340721.

17: Plateau P, Mayaux JF, Blanquet S. Zinc(II)-dependent synthesis of diadenosine 5', 5"' -P(1) ,P(4) -tetraphosphate by Escherichia coli and yeast phenylalanyl transfer ribonucleic acid synthetases. Biochemistry. 1981 Aug 4;20(16):4654-62. PubMed PMID: 7028092.

18: Thiebe R. Catalytical mechanism of the phenylalanyl-tRNA synthetase from yeast. Reactivity of ATP in the absence of phenylalanine. Eur J Biochem. 1984 Apr 2;140(1):143-6. PubMed PMID: 6368229.

19: Baltzinger M, Holler E. Kinetics of acyl transfer ribonucleic acid complexes of Escherichia coli phenylalanyl-tRNA synthetase. A conformational change is rate limiting in catalysis. Biochemistry. 1982 May 11;21(10):2460-7. PubMed PMID: 7046786.

20: Illangasekare M, Yarus M. Small-molecule-substrate interactions with a self-aminoacylating ribozyme. J Mol Biol. 1997 May 9;268(3):631-9. PubMed PMID: 9171286.